Part C. Who Else Has My Compound?
Suggested compounds for unknowns. All compounds should be colorless, and samples should be
numbered in such a way that they cannot easily be decoded. Samples should be dispensed such that there
are two or three students per compound in the lab.
Quantity/3 students
Acetanilide

To prepare chromic acid, add 1 g of chromic anhydride to 1 mL of concentrated H2SO4
and stir the mixture until a smooth paste is obtained. Then cautiously dilute the paste with
3 mL of distilled H2O and stir this mixture until a clear orange solution is obtained.
CH 5 Extraction
5.3

39
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whole or in part.

Section 2. Chemicals and Special Equipment by Chapters

Experimental Organic Chemistry: A Miniscale and Microscale Approach

Part B. Identifying Unknown Esters Produced by Fischer Esterification (cont.)
Programmable GC Methods:
General GC: PE Model Clarus 580 Gas Chromatograph; Restek Column (15 or 30 M) Rtx-1
Crossbonded 100% Dimethyl polysiloxane (0.32 ID; 0.25 df). Standards were run for the analysis each
day, and retention times are reported in min.
Three programmable GC methods may be used to separate the two families of esters. Method A is used
for the rapid analysis of propanoic esters. Method B for the rapid analysis of alkyl benzoates, and
Method C may be used to separate all eight compounds in a single run.
TABLE 3: RETENTION TIMES (in min) for Propanoate Esters

To prepare the reagent, two stock solutions must be combined at the time the test is being performed.
Prepare solution A is by dissolving 2.5 g of silver nitrate in 43 mL of distilled H2O. Prepare solution B
by dissolving 3 g of KOH in 42 mL of distilled H2O.
Benedict’s Test
Chemicals:

Quantity

Sodium citrate, dihydrate

26 g

Sodium carbonate, anhydrous

15 g

Cupric sulfate

2.6 g

Barfoed’s Test
Chemicals:
Cupric acetate
Acetic acid, glacial

Quantity
6g
0.9 mL

Formation of Osazones
Chemicals:
D-Glucose, D-fructose, sucrose

Sodium bisulfite
Ethanol, 95%

Quantity
2 g of each
10 g
150 mL

46
2016 Cengage Learning. All rights Reserved. May not be scanned, copied, or duplicated, or posted to a publicly accessible website, in
whole or in part.

48
2016 Cengage Learning. All rights Reserved. May not be scanned, copied, or duplicated, or posted to a publicly accessible website, in
whole or in part.

Section 2. Chemicals and Special Equipment by Chapters

Experimental Organic Chemistry: A Miniscale and Microscale Approach

CH 25 Identifying Organic Compounds
Chemicals:

This is a partial list of chemicals and solutions, with common acids, bases, and organic
solvents not being included. In cases where directions are provided for preparing solutions,
the amounts are to serve approximately 10 students unless otherwise noted.

Acetic anhydride
Aniline
Baeyer reagent
To prepare 0.1 M aqueous KMnO4, dissolve 0.32 g of potassium permanganate in 20 mL of distilled
H2O. This amount of solution should suffice for the needs of aboujt 100 students.
Benzenesulfonyl chloride
Benzoyl chloride
Bromine in dichloromethane
To prepare a 0.1 M solution, dissolve 0.1 mL of Br2 in 20 mL of CH2Cl2; keep the solution in a tightly
stoppered container. This amount of solution should suffice for the needs of about 100 students.
Bromine-potassium bromide reagent
To prepare the reagent, dissolve 2 g of KBr in 12 mL of distilled water and adding 0.6 mL of Br2.
Bromine water
To prepare the saturated solution, dissolve 11.8 mL of Br2 in 10 mL of H2O.
Ceric ammonium nitrate
To prepare the reagent, dissolve 2 g of ceric ammonium nitrate in 5 mL of 2 M nitric acid; the
dissolution is hastened by heating.
Chromic anhydride
To prepare chromic acid, add 10 g of chromic anhydride to 10 mL of concentrated H2SO4 and stir the
mixture until a smooth paste is obtained. The cautiously dilute the paste with 30 mL of distilled H2O
and stir this mixture until a clear orange solution is obtained.
Diethylene glycol
3,5-Dinitrobenzoic acid
3,5-Dinitrobenzoyl chloride
2,4-Dinitrophenylhydrazine
To prepare the solution for qualitative tests and for making 2,4-dinitrophenylhydrazones, dissolve 2 g
of 2,4-dinitrophenylhydrazine in 10 mL of concentrated H2SO4; add this solution, with stirring, to a
solution of 15 mL of distilled H2O and 50 mL of 95% ethanol. Vigorously stir this solution and then
filter it to remove any undissolved solids.
Ferric chloride
To prepare a 0.2 M aqueous FeCl3 solution, dissolve 5.4 g of ferric chloride hexahydrate in 100 mL of
distilled water.

This amount of solution should suffice for the needs of about 100 students.

49
2016 Cengage Learning. All rights Reserved. May not be scanned, copied, or duplicated, or posted to a publicly accessible website,
in whole or in part.

Corrosive material, convulsions, muscle Do not eat or drink in Wash out mouth with
weakness, and symptoms as described in the laboratory.
water; if vomiting occurs,
acute ingestion.
keep head lower than hips.
Seek medical advice
immediately.

Carcinogenicity

Not a known carcinogen.

Mutagenicity

Remove from exposure
immediately and seek
medical advice.

Thoroughly flush eyes
with water for several min,
removing contact lenses if
possible, and seek medical
advice.

Not a known mutagen.

For more detailed information, consult the Material Safety Data Sheet for this compound.
Abbreviations: